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3,5-Xylidin

3,5-Dimethylaniline

HCID 7949
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Grundinformationen

CAS
108-69-0
Standard-SMILES
Cc1cc(C)cc(N)c1
InChIKey
MKARNSWMMBGSHX-UHFFFAOYSA-N
Summenformel
C8H11N
Durchschnittliche Molmasse
121,18 g/mol
Monoisotopische Masse
121,08914936

Überblick

3,5-xylidine is a dark brown liquid. (NTP, 1992)

Namen und Bezeichner

Bevorzugter Name
3,5-Dimethylaniline
IUPAC
3,5-dimethylaniline
Lokaler Name
3,5-Xylidin
Englischer Name
3,5-Dimethylaniline
Summenformel
C8H11N
Molmasse
121.18

Namen und Synonyme

3,5-Dimethylaniline108-69-03,5-XYLIDINEBenzenamine, 3,5-dimethyl-1-Amino-3,5-dimethylbenzene3,5-Xylylamine3,5-Dimethylbenzenamine3,5-Dimethylphenylamine5-Amino-1,3-xylene3,5-Dimethylbenzeneamine5-Amino-m-xylene5-Amino-1,3-dimethylbenzene
Weitere Namen anzeigen
3,5-XylidinSincerity-MA3,5-XylideneAKOS BBS-00003574
Benzene, 1-amino-3,5-dimethyl-DTXSID80263091418BR6T2HNSC-26880DTXCID8063093,5-DMA cpdRefChem:91596203-607-0

Datenbank-Bezeichner

CAS
108-69-0
PubChem CID
7949
DTXSID
DTXSID8026309
ChEMBL
CHEMBL1603782
UNII
1418BR6T2H
EC Number
203-607-0
Nikkaji
J2.426K

Eigenschaften

Berechnete StruktureigenschaftenWird ergänzt

XLogP
2
Polarare Oberfläche (TPSA)
26 Ų
H-Brücken-Donoren
1
H-Brücken-Akzeptoren
1
Frei drehbare Bindungen
0
Schwere Atome
9
Formalladung
0
Komplexität
80,6

Experimentelle und physikochemische Eigenschaften

Chemical ClassesNitrogen Compounds -> Amines, Aromatic
SpringerMaterials Properties13C nuclear magnetic resonance spectrum
LogP2.09
Density · 3 Einträge

0.9706 at 68 °F (NTP, 1992) - Less dense than water; will float

0.9706 @ 20 °C/4 °C

Relative density (water = 1): 0.97

Color/FormOily liquid
Solubility · 3 Einträge

less than 1 mg/mL at 66 °F (NTP, 1992)

Sol in ether, carbon tetrachloride; slightly soluble in water

Solubility in water, g/100ml at 20 °C: 0.48

Flash Point · 3 Einträge

200 °F (NTP, 1992)

97 °C (206 °F) (Closed cup)

93 °C

Boiling Point · 3 Einträge

428 to 430 °F at 760 mmHg (NTP, 1992)

220.5 °C

220 °C

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

GHS-Klassifizierung

GHS Classification · 6 Einträge

Danger

H301+H311+H331 (68.5%): Toxic if swallowed, in contact with skin or if inhaled [Danger Acute toxicity, oral; acute toxicity, dermal; acute toxicity, inhalation]

P260, P261, P262, P264, P270, P271, P273, P280, P301+P316, P302+P352, P304+P340, P316, P319, P321, P330, P361+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 162 reports by companies from 13 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Danger

H302: Harmful if swallowed [Warning Acute toxicity, oral]

Gefahrenhinweise

Regulatory Information · 2 Einträge

Chemical: Benzenamine, 3,5-dimethyl-

REACH registered substance: 3,5-xylidine (EC: 203-607-0)

Other Safety InformationIMAP assessments - Xylidines: Human health tier II assessment
DOT LabelExplosive 1.3C Poison
Fire Hazards · 2 Einträge

This chemical is combustible. (NTP, 1992)

Combustible. Gives off irritating or toxic fumes (or gases) in a fire. Above 93 °C explosive vapour/air mixtures may be formed.

Health HazardsSYMPTOMS: Symptoms of exposure to this compound may include headaches, drowsiness, cyanosis, mental confusion, convulsions, nervous system and blood effects, fatigue, loss of appetite and dizziness.
Hazards Summary · 2 Einträge

Heavy exposure can cause methemoglobinemia and lowering of consciousness; Chronic exposure may cause anemia; Can be absorbed through skin; [ICSC] Erythrocyte hemolysis, significantly increased methemoglobin levels, and liver and kidney injury observed in sub-chronic oral studies of rats; May cause irritation, headache, drowsiness, cyanosis, confusion, convulsions, and other nervous system and blood effects; [NTP] Toxic by ingestion, inhalation, and skin absorption; Prolonged or repeated exposure may cause kidney and liver injury; [ECHA REACH Registrations] An irritant; Toxic by ingestion, inhalation, and skin absorption; May induce methemoglobinemia; [Alfa Aesar MSDS] See Xylidine, mixed isomers.

Chemie und Industrie

Verwendung und Herstellung

Uses · 2 Einträge

Used mainly in dye manufacture; Also used as reagents in synthetic organic chemistry; [Merck Index] Used to make pharmaceuticals, azo dyes, curing agents, antioxidants, antiozonants, additives and detergents for gasoline, wood preservatives, wetting agents for textiles, frothing agents for ore dressing, special lacquers, and metal complexers; [NTP] Used to make fine chemicals; [ECHA REACH Registrations]

Used as a chemical intermediate for the synthesis of Pigment Red 149.

U.S. Production · 2 Einträge

(1972) NOT PRODUCED COMMERCIALLY IN USA

(1975) NOT PRODUCED COMMERCIALLY IN USA

Methods of Manufacturing · 2 Einträge

NITRATION AND REDUCTION OF XYLENE FOLLOWED BY THE SEPARATION OF THE 3,5- ISOMER BY CONVERSION TO THE FORMYL DERIVATIVE WHICH IS THEN HYDROLYZED TO THE FREE BASE

3,5-xylenol + ammonia (ammoniation)

General Manufacturing InformationBenzenamine, 3,5-dimethyl-: ACTIVE
Anwendungen · 1 Eintrag

Verwenden3,5-Dimethylaniline is the reagent commonly useful in the manufacture of dyes. It undergoes polymerization in the presence of cerium(IV) sulfate as an oxidant. This compound was also employed to produce chiral packing materials for high performance liquid chromatography.

Vor- und nachgelagerte Produkte

Vorgelagerte Rohstoffe

3,5-Xylenol5-Bromo-m-xylene

Nachgelagerte Produkte

3,5-DIMETHYLPHENYL ISOTHIOCYANATE

Zugehörige Reaktionen

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Reaktionsgleichung von HRID 92055
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Decomposition
WHEN HEATED TO DECOMP, XYLIDINES EMIT HIGHLY TOXIC FUMES. /XYLIDINES/
Melting Point · 3 Einträge

49.6 °F (NTP, 1992)

9.8 °C

9.8 °C

Vapor DensityRelative vapor density (air = 1): 4.19
Odor Threshold · 2 Einträge

Odor threshold in air= 1.00X10+12 molecules/cc /Xylidines/

Low threshold= 0.0240 mg/cu m; High threshold= 0.0240 mg/cu m. /Xylidine/

Physikochemische Eigenschaften

Schmelzpunkt
7 · 7-9 °C
Siedepunkt
104 · 104-105 °C14 mm Hg(lit.)
Dichte
0.972 g/mL · 0.972 g/mL at 25 °C(lit.)
Dampfdruck
1.3 · 1.3-27hPa at 20-100℃
Brechungsindex
20 · n20/D 1.557(lit.)
Flammpunkt
200 °F · 200 °F
Aggregatzustand
Liquid
pka
1 · pK1:4.765(+1) (25°C)
Farbe
Clear yellow-brown to brown
Wasserlöslichkeit
0.1 g/100 · <0.1 g/100 mL at 19 ºC
Merck
14 · 14,10084
Specific Activity
50 · 50-60 mCi/mmol
BRN
507051 · 507051
Henry's Law Constant
3.9 · 3.9×100 mol/(m3Pa) at 25℃, HSDB (2015)
InChI
1S/C8H11N/c1-6-3-7(2)5-8(9)4-6/h3-5H,9H2,1-2H3
InChIKey
MKARNSWMMBGSHX-UHFFFAOYSA-N
SMILES
Cc1cc(C)cc(N)c1
CAS Datenbank
108 · 108-69-0(CAS DataBase Reference)
NIST chemische Informationen
3 · Benzenamine, 3,5-dimethyl-(108-69-0)
EPA chemische Informationen
3 · 3,5-Dimethylaniline (108-69-0)

The major hazards encountered in the use and handling of 3,5-xylidine stem from its toxicologic properties. Toxic by all routes (ie, inhalation, ingestion, and dermal absorption), exposure to this oil may occur from its use as a chemical intermediate for the production of dyes. Contact with 3,5-xylidine may cause burns to the skin and eyes. Death is also a possible outcome from exposure. While the OSHA PEL is set at a TWA of 5 ppm, the ACGIH lists xylidine (mixed isomers) on its 1988-1989 Notice of Intended Changes with a proposed TLV of 0.5 ppm, and a designation of "suspected human carcinogen". In activities or situations where over-exposure may occur, wear a self-contained breathing apparatus, and full chemical protective clothing which is specifically recommended by the shipper or manufacturer to prevent skin contact with xylidine. If contact should occur, immediately flush the affected skin or eyes with running water for at least 15 minutes. Remove contaminated clothing and shoes at the site. Do not eat or smoke in xylidine work areas. While xylidine does not ignite easily, it can burn with the production of irritating or poisonous gases. Also, containers may explode violently in the heat of a fire. Fires involving xylidine may be extinguished with dry chemical, CO2, Halon, or standard foam. Water spray if used, should be applied with caution because it may cause frothing. Fight the fire from a maximum distance and dike runoff from fire control water. Xylidine should be stored away from heat, strong oxidizers, and hypochlorite bleaches. Shipping regulations and other DOT regulatory requirements should be consulted before transport. If xylidine should spill, dike far ahead, then take up with sand or other noncombustible absorbent and place into containers for later disposal. Incineration is a possible form of disposal for xylidine. Before implementing land disposal of waste 3,5-xylidine, consult with environmental regulatory agencies for guidance.

Reactive GroupAmines, Aromatic
EC ClassificationSymbol: T, N; R: 23/24/25-33-51/53; S: (1/2)-28-36/37-45-61
UN ClassificationUN Hazard Class: 6.1; UN Pack Group: II
OSHA Standards · 2 Einträge

Permissible Exposure Limit: Table Z-1 8-hr Time-Weighted Avg: 5 ppm (25 mg/cu m). Skin Designation. /Xylidine/

Vacated 1989 OSHA PEL TWA 2 ppm (10 mg/cu m), skin designation, is still enforced in some states. /Xylidine/

Reactivity Profile · 1 Eintrag

3,5-XYLIDINE ignites on contact with fuming nitric acid (NTP, 1992). Neutralizes acids in exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen may be generated in combination with strong reducing agents, such as hydrides.

Chemical Dangers · 1 Eintrag

Decomposes on burning. This produces toxic and corrosive fumes including nitrogen oxides. Reacts violently with strong oxidants. Reacts with hypochlorites. This produces explosive chloroamines. Reacts with acids, acid anhydrides, acid chlorides and halogens. Attacks plastic and rubber.

Sicherheit und Schutzausrüstung

Fire Fighting · 2 Einträge

Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)

Use water spray, carbon dioxide, foam, powder.

First Aid Measures · 4 Einträge

Fresh air, rest. Refer for medical attention.

Remove contaminated clothes. Rinse and then wash skin with water and soap. Refer for medical attention .

Rinse with plenty of water for several minutes (remove contact lenses if easily possible).

Rinse mouth. Refer for medical attention .

First Aid · 1 Eintrag

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

Safe StorageSeparated from strong oxidants, acids, acid anhydrides, acid chlorides, hypochlorites, halogens and food and feedstuffs. Well closed. Store in an area without drain or sewer access.
Exposure Control and Personal ProtectionBiological Exposure Indices (BEI) [ACGIH] - Methemoglobin in blood = 1.5% of hemoglobin during or at end of shift. [ACGIH]
Fire Fighting Procedures · 2 Einträge

USE WATER SPRAY, DRY CHEMICAL, FOAM, OR CO2; WEAR FULL PROTECTIVE CLOTHING. /XYLIDINES/

If material on fire or involved in fire: Extinguish fire using agent suitable for type of surrounding fire. (Material itself does not burn or burns with difficulty.) Use water in flooding quantities as fog. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. /Xylidines/

Cleanup Methods · 2 Einträge

Environmental considerations - land spill: Dig a pit, pond, lagoon, holding area to contain liquid or solid material. /SRP: If time permits, pits, ponds, lagoons, soak holes, or holding areas should be sealed with an impermeable flexible membrane liner./ Dike surface flow using soil, sand bags, foamed polyurethane, or foamed concrete. Absorb bulk liquid with fly ash, cement powder, or commercial sorbents. /Xylidines/

Environmental considerations - water spill: Use natural barriers or oil spill control booms to limit spill travel. Remove trapped material with suction hoses. /Xylidines/

Nonfire Spill Response · 1 Eintrag

SMALL SPILLS AND LEAKAGE: If you spill this chemical, FIRST REMOVE ALL SOURCES OF IGNITION. Then, use absorbent paper to pick up all liquid spill material. Your contaminated clothing and absorbent paper should be sealed in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 60-70% ethanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.

Disposal Methods · 2 Einträge

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Disposal methods: incineration. A). Dissolve in such combustible solvent as alcohols, benzene, etc. Spray solvent into the furnace with afterburner and scrubber. B). Pour into a mixture of sand and soda ash (9:1). After mixing, put into a paper carton stuffed full with packing paper to serve as fuel. Burn in the furnace. /Xylidines/

Spillage Disposal · 1 Eintrag

Personal protection: chemical protection suit and filter respirator for organic gases and vapours adapted to the airborne concentration of the substance. Do NOT let this chemical enter the environment. Collect leaking and spilled liquid in sealable containers as far as possible. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations.

Preventive Measures · 5 Einträge

SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.

Non-impervious clothing which becomes contaminated with xylidine should be t removed immediately and not reworn until the xylidine is removed from the clothing. /Xylidines/

Eating and smoking should not be permitted in areas where liquid xylidine is handled, processed, or stored. /Xylidines/

Employees who handle liquid xylidine should wash their hands thoroughly with soap or mild detergent and water before eating, smoking, or using toilet facilities. /Xylidines/

For more Preventive Measures (Complete) data for 3,5-XYLIDINE (7 total), please visit the HSDB record page.

Isolation and EvacuationExcerpt from ERG Guide 112 [Explosives - Division 1.1, 1.2, 1.3 or 1.5]:

Toxikologische Informationen

Body Burden · 1 Eintrag

Seven of forty-six human adipose tissue samples (positive samples all within the 45 yr and above age bracket; 4 positive samples collected from the north-central region, 1 sample from the south and 2 samples from the west) contained 3,5-xylidine at unreported concentrations(1).

Environmental Fate · 3 Einträge

TERRESTRIAL FATE: Based on a recommended classification scheme(1), an estimated Koc value of 120(SRC), determined from a structure estimation method(2), indicates that 3,5-xylidine will have high mobility in soil(SRC). However, anilines are expected to bind stongly to humus or soil organic matter in soils due to the high reactivity of the aromatic amino group(3,4), suggesting that mobility may be much lower in some soils(SRC). Volatilization of 3,5-xylidine may be important from moist soil surfaces(SRC) given an estimated Henry's Law constant of 2.5X10-6 atm-cu m/mole(SRC), using a fragment constant estimation method(5). Based on limited aqueous screening study data, 3,5-xylidine may rapidly biodegrade under aerobic conditions in soil(SRC); 3,5-xylidine was degraded by 53% in 6 hours using an activated sludge inoculum(6).

AQUATIC FATE: Based on a recommended classification scheme(1), an estimated Koc value of 120(SRC), determined from a structure estimation method(2), indicates that 3,5-xylidine should not adsorb to suspended solids and sediment in water(SRC). However, aromatic amine groups are recognized as having a strong affinity to organic carbon, suggesting that this compound may bind strongly to suspended organic material in water(3,4). 3,5-Xylidine may volatilize from water surfaces(1,SRC) based on an estimated Henry's Law constant of 2.5X10-6 atm-cu m/mole(SRC), developed using a fragment constant estimation method(5). Estimated volatilization half-lives for a model river and model lake are 16 and 120 days, respectively(1,SRC), although adsorption onto organic material may attenuate this process(SRC). According to a classification scheme(7), an estimated BCF value of 26(1,SRC), from an estimated log Kow of 2.2(6,SRC), suggests that bioconcentration in aquatic organisms is low(SRC). Based on limited aqueous screening study data, 3,5-xylidine may rapidly biodegrade under aerobic conditions in water(SRC); 3,5-xylidine was degraded by 53% in 6 hours using an activated sludge inoculum(8). As a class, aromatic amines react relatively rapidly in sunlit natural water via reaction with photochemically-produced hydroxyl radicals and peroxy radicals(9); typical half-lives for peroxy and hydroxy radical reactions are on the order of 19 and 30 sunlight hours, respectively(9).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 3,5-xylidine, which has an estimated vapor pressure of 0.13 mm Hg at 25 °C(2,SRC), should exist solely as a vapor in the ambient atmosphere. Vapor-phase 3,5-xylidine may be degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be about 2 hours(3,SRC).

Adverse EffectsOccupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.
Exposure RoutesThe substance can be absorbed into the body in hazardous amounts by inhalation, through the skin and by ingestion.
Signs and Symptoms · 3 Einträge

Dizziness. Drowsiness. Headache. Nausea.

MAY BE ABSORBED! See Ingestion.

Blue lips, fingernails and skin. Dizziness. Drowsiness. Headache. Nausea. Unconsciousness.

ICSC Environmental DataThis substance may be hazardous to the environment. Special attention should be given to aquatic organisms.
Medical Surveillance · 1 Eintrag

Initial medical examination: A complete history & physical examination. The purpose is to detect existing conditions that might place the exposed employee at increased risk, and to establish a baseline for future health monitoring. Exam of the blood, lung, liver, kidneys, and cardiovascular system should be stressed. ... Periodic medical exam ... should be repeated on an annual basis. /Xylidine/

Soil Adsorption/Mobility · 1 Eintrag

Using a structure estimation method based on molecular connectivity indices(1), the Koc for 3,5-xylidine can be estimated to be about 120(SRC). According to a recommended classification scheme(2), this estimated Koc value suggests that 3,5-xylidine has high mobility in soil(SRC). However, anilines are expected to bind stongly to humus or soil organic matter in soils due to the high reactivity of the aromatic amino group(3,4). Low adsorption is observed at a neutral pH with pure clay minerals or soils for substituted anilines(4).

Artificial Pollution Sources3,5-Xylidine's production and subsequent use in the manufacture of azo dyes(1) may result in its release to the environment through various waste streams(SRC).
Environmental Biodegradation · 1 Eintrag

3,5-Xylidine, initially present at 20 mg/l, was 53% degraded in 6 hours using an activated sludge inoculum under aerobic conditions(1). E. coli converted 3,5-xylidine to the corresponding (phenylazo)naphthol in the presence of nitrate with this reaction proceeding within 24 hours(2).

Environmental Bioconcentration · 1 Eintrag

An estimated BCF value of 26 was calculated for 3,5-xylidine(SRC), using an estimated log Kow of 2.2(1,SRC) and a recommended regression-derived equation(2). According to a classification scheme(3), this BCF value suggests that bioconcentration in aquatic organisms is low(SRC).

Volatilization from Water/Soil · 1 Eintrag

The Henry's Law constant for 3,5-xylidine is estimated as 2.5X10-6 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This value indicates that 3,5-xylidine will volatilize from water surfaces(2,SRC). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec) is estimated as approximately 16 days(2,SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec) is estimated as approximately 120 days(2,SRC). Adsorption to organic material may attenuate this process(SRC). The Henry's Law constant value for 3,5-xylidine(1,SRC) indicates that volatilization from moist soil surfaces may occur(SRC).

Sicherheitsdaten

F
8
wgk
3
tsca
TSCA listed
ridadr
UN 1711 6.1/PG 2
hs_code
29214990
RTECS-Nr.
ZE9625000
risk_code
23/24/25-33-51/53
hazard_code
T,N
hazard_note
Toxic
safety_code
28-36/37-45-61-28A
hazard_class
6.1
packing_group
II
Speicherklasse
6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
Giftige Stoffe Daten
108-69-0(Hazardous Substances Data)
Hazard Classifications
Acute Tox. 3 DermalAcute Tox. 3 InhalationAcute Tox. 3 OralAquatic Chronic 2STOT RE 2
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