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3-Chlorpropionitril

3-Chloropropionitrile

HCID 10963
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Grundinformationen

CAS
542-76-7
Standard-SMILES
N#CCCCl
InChIKey
GNHMRTZZNHZDDM-UHFFFAOYSA-N
Summenformel
C3H4ClN
Durchschnittliche Molmasse
89,52 g/mol
Monoisotopische Masse
89,00322681

Überblick

Propionitrile, 3-chloro- is a colorless liquid with a characteristic acrid odor. Used in pharmaceutical and polymer synthesis. (EPA, 1998)

Namen und Bezeichner

Bevorzugter Name
3-Chloropropionitrile
IUPAC
3-chloropropanenitrile
Lokaler Name
3-Chlorpropionitril
Englischer Name
3-Chloropropiononitrile
Summenformel
C3H4ClN
Molmasse
89.52

Namen und Synonyme

3-Chloropropionitrile3-Chloropropanenitrile542-76-73-ChloropropiononitrilePropanenitrile, 3-chloro-1-Chloro-2-cyanoethane3-CHLOROPROPANONITRILEPropionitrile, 3-chloro-beta-Chloropropionitrile3-ChlorpropannitrilUSAF A-8798RCRA waste number P027
Weitere Namen anzeigen
CH2ClCH2CNusafa-8798rcrawastenumberp0273-choropropionitrile3-Chloropropuinitrile3-chloro-propionitril
.beta.-ChloropropionitrileNSC 2588DTXSID4030336MFCD0000195261N7S4SZ2QNSC-2588DTXCID20103363-Chlorpropannitril [Czech]

Datenbank-Bezeichner

CAS
542-76-7
PubChem CID
10963
DTXSID
DTXSID4030336
ChEMBL
CHEMBL1451739
UNII
61N7S4SZ2Q
EC Number
208-827-0
Nikkaji
J35.375B

Eigenschaften

Berechnete Struktureigenschaften

XLogP
0,2
Polarare Oberfläche (TPSA)
23,8 Ų
H-Brücken-Donoren
0
H-Brücken-Akzeptoren
1
Frei drehbare Bindungen
1
Schwere Atome
5
Formalladung
0
Komplexität
51,2

Experimentelle und physikochemische Eigenschaften

Chemical Classes · 2 Einträge

Nitrogen Compounds -> Nitriles

Flammable agents - 2nd degree

SpringerMaterials PropertiesSchoenflies notation
LogP0.18
OdorACRID CHARACTERISTIC ODOR
Density · 3 Einträge

1.1573 at 68 °F (EPA, 1998) - Denser than water; will sink

1.1573 @ 20 °C

1.1363 @25 °C

Color/FormCOLORLESS LIQ
Solubility · 3 Einträge

MISCIBLE WITH ACETONE, BENZENE, CARBON TETRACHLORIDE, ALC, ETHER

Water solubility: 4.5 g/100 ml at 25 °C

Solubility of water in beta-chloropropionitrile: 2.2 ml/100 g at 25 °C.

Flash Point · 3 Einträge

168 °F (EPA, 1998)

75.5 °C

168 °F (CLOSED CUP)

Boiling Point · 3 Einträge

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

H300 (93.8%): Fatal if swallowed [Danger Acute toxicity, oral]

P261, P264, P264+P265, P270, P271, P280, P301+P316, P302+P352, P304+P340, P305+P351+P338, P316, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 48 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Danger

H227: Combustible liquid [Warning Flammable liquids]

Gefahrenhinweise

Regulatory Information · 2 Einträge

3-Chloropropionitrile: Does not have an individual approval but may be used under an appropriate group standard

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

DOT LabelPoison
Fire HazardsToxic gas (hydrogen chloride) is released when the compound is heated above 266F. When heated to decomposition, it emits very toxic fumes of chlorine- containing compounds and nitrogen oxides. Avoid heat. (EPA, 1998)
Fire PotentialFire hazard: Moderate, in its liquid form when exposed to heat or flame.
Health Hazards · 1 Eintrag

Toxic effects are a result of systemic cyanide poisoning. (Non-Specific -- Cyanide) Few poisons are more rapidly lethal. Average oral lethal dose for hydrogen cyanide is approximately 60-90 mg (corresponds to 200 mg of potassium cyanide). Cause of death is lack of oxygen to the body's cells (especially the brain and heart) as a result of the chemical inhibiting cell enzymes. (EPA, 1998)

Chemie und Industrie

Pharmakologische Informationen

Absorption, Distribution and ExcretionIT IS PROBABLY ABSORBED THROUGH THE INTACT SKIN.

Verwendung und Herstellung

Uses · 2 Einträge

Used in pharmaceutical and polymer synthesis; [Merck Index]

IN PHARMACEUTICAL & POLYMER SYNTHESIS; COMBINES THE REACTIVITY OF NITRILE & AN ALKYL HALIDE.

U.S. Exports(1984) 9.73X10+9 g /Nitriles and their derivatives/
U.S. Imports(1984) 9.27X10+10 g /Nitriles, NSPF/
Methods of ManufacturingPREPD FROM ACRYLONITRILE & HYDROGEN CHLORIDE ... .
General Manufacturing InformationPropanenitrile, 3-chloro-: ACTIVE

Anwendungen

VerwendenIn pharmaceutical and polymer synthesis. Combines the reactivity of a nitrile and an alkyl halide. Because of the cyano group the chlorine atom is more reactive than in ordinary alkyl halides.

Vor- und nachgelagerte Produkte

Vorgelagerte Rohstoffe

Acrylnitril

Nachgelagerte Produkte

5,6-dihydro-2-nitro-7H-Pyrrolo[1,2-a]iMidazol-7-onePyrrolidin-1-propiononitril

Zugehörige Reaktionen

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HRID 35604als Eduktuspto-grants-1988_08
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Reaktionsgleichung von HRID 569275
HRID 569275als Eduktuspto-grants-1988_03
Reaktionsgleichung von HRID 597392
HRID 597392als Eduktuspto-grants-1977_03
Reaktionsgleichung von HRID 655256
HRID 655256als Eduktuspto-grants-2011_12
Reaktionsgleichung von HRID 670602
HRID 670602als EduktTraining data from https://doi.org/10.1039/C8SC04228D (3/10)
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347 to 349 °F at 760 mmHg (EPA, 1998)

175-176 °C

176 °C @760 [mm Hg]

DecompositionBEGINS TO DECOMP WHEN HEATED ABOVE 130 °C EVOLVING HYDROGEN CHLORIDE
Melting Point · 3 Einträge

-60 °F (EPA, 1998)

-51 °C

-51 °C

Vapor Density3 (EPA, 1998) - Heavier than air; will sink (Relative to Air)

Physikochemische Eigenschaften

Schmelzpunkt
-52 · -52--50 °C (lit.)
Siedepunkt
174 · 174-176 °C (lit.)
Dichte
1.144 g/mL · 1.144 g/mL at 25 °C (lit.)
Brechungsindex
20 · n20/D 1.438(lit.)
Flammpunkt
168 °F · 168 °F
storage temp.
30 °C · Store below +30°C.
Löslichkeit
45 g/l · 45g/l
Aggregatzustand
clear liquid
Farbe
Colorless to Almost colorless
Wasserlöslichkeit
4.5 g/100 · 4.50 g/100 mL
Merck
14 · 14,2160
BRN
1098454 · 1098454
InChI
1S/C3H4ClN/c4-2-1-3-5/h1-2H2
InChIKey
GNHMRTZZNHZDDM-UHFFFAOYSA-N
SMILES
ClCCC#N
CAS Datenbank
542 · 542-76-7(CAS DataBase Reference)
NIST chemische Informationen
2 · Cl(CH2)2CN(542-76-7)
EPA chemische Informationen
3 · 3-Chloropropionitrile (542-76-7)
Hazards Summary · 1 Eintrag

No poisoning cases reported, but expected to be similar to cyanide poisoning from propionitrile with rapid loss of consciousness; [HSDB] Absorbed through skin causing systemic cyanide poisoning; [Merck Index] An irritant; [MSDSonline] See NITRILES.

Reactive GroupHalogenated Organic Compounds
RCRA Requirements · 1 Eintrag

P027; As stipulated in 40 CFR 261.33, when 3-chloropropionitrile, as a commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate, becomes a waste, it must be managed according to federal and/or state hazardous waste regulations. Also defined as a hazardous waste is any container or inner liner used to hold this waste or any residue, contaminated soil, water, or other debris resulting from the cleanup of a spill, into water or on dry land, of this waste. Generators of small quantities of this waste may qualify for partial exclusion from hazardous waste regulations (40 CFR 261.5(e)).

Reactivity ProfileToxic gas (hydrogen chloride) is released when the compound is heated above 266 F. When heated to decomposition, it emits very toxic fumes of chlorine- containing compounds and nitrogen oxides. Avoid heat. [EPA, 1998].
Air and Water ReactionsNo rapid reaction with air. No rapid reaction with water.
EPA Hazardous Waste NumberP027; An acute hazardous waste when a discarded commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate.
NFPA Hazard Classification · 3 Einträge

0 - Materials that, under emergency conditions, would offer no hazard beyond that of ordinary combustible materials.

2 - Materials that must be moderately heated or exposed to relatively high ambient temperatures before ignition can occur. Materials would not under normal conditions form hazardous atmospheres with air, but under high ambient temperatures or under moderate heating could release vapor in sufficient quantities to produce hazardous atmospheres with air.

1 - Materials that in themselves are normally stable but that can become unstable at elevated temperatures and pressures.

Sicherheit und Schutzausrüstung

Fire Fighting(Non-Specific -- Propionitrile) Wear positive pressure breathing apparatus and special protective clothing. Isolate for 1/2 mile in all directions if tank car or truck is involved in fire.
First AidWarning: Effects, including skin reactions, may be delayed. Caution is advised. Vital signs should be monitored closely. Heart palpitation may begin within minutes after exposure.
Exposure Control and Personal Protection · 1 Eintrag

TIH (Toxic Inhalation Hazard) - Term used to describe gases and volatile liquids that are toxic when inhaled. Some are TIH materials themselves, e.g., chlorine, and some release TIH gases when spilled in water, e.g., chlorosilanes. [ERG 2016].

Nonfire Spill Response · 1 Eintrag

(Non-Specific -- Propionitrile) Do not touch spilled material; stop leak if you can do so without risk. Use water spray to reduce vapors. Absorb small spills with sand or other noncombustible absorbent material. Dike far ahead of spill for later disposal. Isolate hazard area and deny entry. Stay upwind. (EPA, 1998)

Disposal Methods · 2 Einträge

Generators of waste (equal to or greater than 100 kg/mo) containing this contaminant, EPA hazardous waste number P027, must conform with USEPA regulations in storage, transportation, treatment and disposal of waste.

A potential candidate for liquid injection incineration at a temperature range of 650 to 1,600 °C and a residence time of 0.1 to 2 seconds. A potential candidate for rotary kiln incineration at a temperature range of 820 to 1,600 °C and residence times of seconds for liquids and gases, and hours for solids.

Preventive Measures... SHOULD BE HANDLED WITH CAUTION & ALL EXPOSED PERSONS CLOSELY FOLLOWED MEDICALLY.
Isolation and EvacuationExcerpt from ERG Guide 151 [Substances - Toxic (Non-Combustible)]:
Protective Action Criteria (PAC) · 3 Einträge

0.030 [mg/m3]

0.33 [mg/m3]

2.0 [mg/m3]

Personal Protective Equipment (PPE) · 6 Einträge

For emergency situations, wear a positive pressure, pressure-demand, full facepiece self-contained breathing apparatus (SCBA) or pressure- demand supplied air respirator with escape SCBA and a fully-encapsulating, chemical resistant suit. (EPA, 1998)

Wear appropriate equipment to prevent: Any possibility of skin contact. /Cyanides/

Wear eye protection to prevent: Any possibility of eye contact. /Cyanides/

The following equipment should be available: Eyewash, quick drench. /Cyanides/

Recommendations for respirator selection. Max concn for use: 50 mg/cu m: Respirator Classes: Any supplied-air respirator. Any self-contained breathing apparatus. /Cyanides/

For more Personal Protective Equipment (PPE) (Complete) data for 3-CHLOROPROPANONITRILE (6 total), please visit the HSDB record page.

Toxikologische Informationen

Adverse EffectsOther Poison - Chemical Asphyxiant
Medical Surveillance · 2 Einträge

Initial medical examination /should include/: a complete history and physical examination ... to detect existing conditions that might place the exposed employee at incr risk & to establish a baseline for future health monitoring. ... Examination of cardiovascular, nervous, & upper resp systems, & thyroid should be stressed. The skin should be exam for evidence of chronic disorders. ... The aforementioned medical exam should be repeated on an annual basis. ... /Cyanides/

Pre-placement and periodic examinations should include the cardiovascular and central nervous systems, liver and kidney function, blood, history of fainting and dizzy spells. Blood cyanide levels may be useful during acute intoxication. Urinary thiocyanate levels have been used but are nonspecific and are elevated in smokers. /Cyanides/

Human Toxicity Excerpts · 4 Einträge

READILY PENETRATES SKIN TO PRODUCE SYSTEMIC CYANIDE POISONING, DEATH.

SYMPTOMATOLOGY: 1) MASSIVE DOSES MAY PRODUCE, WITHOUT WARNING, SUDDEN LOSS OF CONSCIOUSNESS & PROMPT DEATH FROM RESP ARREST. WITH SMALLER BUT STILL LETHAL DOSES, ILLNESS MAY BE PROLONGED FOR 1 OR MORE HOURS. 2) UPON INGESTION, BITTER ... BURNING TASTE IS SOMETIMES NOTED, FOLLOWED BY FEELING OF CONSTRICTION OR NUMBNESS IN THROAT. SALIVATION & NAUSEA ARE NOT UNUSUAL, BUT VOMITING RARELY OCCURS ... . 3) ANXIETY, CONFUSION, VERTIGO, GIDDINESS & OTHER SENSATION OF STIFFNESS IN LOWER JAW. 4) HYPERPNEA & DYSPNEA. 5) ODOR OF BITTER ALMONDS MAY BE NOTED ON BREATH OR VOMITUS ... . 6) IN EARLY PHASES OF POISONING, INCR IN VASOCONSTRICTOR TONE CAUSES RISE IN BLOOD PRESSURE & REFLEX SLOWING OF HEART RATE. THEREAFTER PULSE BECOMES WEAK AND SOMETIMES IRREGULAR. 6) ... SENSATION OF CONSTRICTION IN CHEST. 7) UNCONSCIOUSNESS, FOLLOWED PROMPTLY BY VIOLENT CONVULSIONS, EPILEPTIFORM OR TONIC ... OPISTHOTONOS & TRISMUS MAY DEVELOP. INVOLUNTARY MICTURITION & DEFECATION OCCUR. 8) PARALYSIS, ... SKIN IS COVERED WITH SWEAT. EYEBALLS PROTRUDE & PUPILS ARE DILATED & UNREACTIVE. MOUTH IS COVERED WITH FOAM WHICH IS SOMETIMES BLOOD-STAINED. SKIN COLOR MAY BE BRICK-RED. CYANOSIS IS NOT PROMINENT IN SPITE OF WEAK & IRREGULAR GASPING. /CYANIDE/

TOXIC BY INGESTION, INHALATION & SKIN CONTACT.

Chloropropanes and chloropropenes cause contact dermatitis, headaches, vertigo, tearing, irritation of mucous membranes, and when ingested, liver damage in humans. /Chloropropanes and chloropropenes/

Non-Human Toxicity ExcerptsSYMPTOMS ARE THOSE OF DEEP ANESTHESIA WITH NO DEMONSTRABLE PATHOLOGY.
Antidote and Emergency Treatment · 1 Eintrag

/Experimental Therapy:/ An approach to antidote therapy for cyanide poisoning by using Stroma-Free Methemoglobin Solution was investigated. Rats injected with an LD100 intravenous dose of cyanide were treated with Stroma-Free Methemoglobin Solution equal to 1.5% of their total body hemoglobin. There was a highly significant increase in the survival rate of the treated group compared to saline controls. The potential advantages of Stroma-Free Methemoglobin Solution over current antidotes include an immediate onset of action, rapid elimination of cyanide from the body and a mode of action that doesn't compromise any of the patients' oxygen carrying capacity. Stroma-Free Methemoglobin Solution shows promise as a significant adjunct in the treatment of cyanide poisoning.

Regulatorische Informationen

RCRA Requirements · 1 Eintrag

P027; As stipulated in 40 CFR 261.33, when 3-chloropropionitrile, as a commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate, becomes a waste, it must be managed according to federal and/or state hazardous waste regulations. Also defined as a hazardous waste is any container or inner liner used to hold this waste or any residue, contaminated soil, water, or other debris resulting from the cleanup of a spill, into water or on dry land, of this waste. Generators of small quantities of this waste may qualify for partial exclusion from hazardous waste regulations (40 CFR 261.5(e)).

CERCLA Reportable Quantities · 2 Einträge

Persons in charge of vessels or facilities are required to notify the National Response Center (NRC) immediately, when there is a release of this designated hazardous substance, in an amount equal to or greater than its reportable quantity of 1,000 lb or 454 kg. The toll free number of the NRC is (800) 424-8802; In the Washington D.C. metropolitan area (202) 426-2675. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV. D.3.b).

Releases of CERCLA hazardous substances are subject to the release reporting requirement of CERCLA section 103, codified at 40 CFR part 302, in addition to the requirements of 40 CFR part 355. Propionitrile, 3-chloro- is an extremely hazardous substance (EHS) subject to reporting requirements when stored in amounts in excess of its threshold planning quantity (TPQ) of 1,000 lbs.

Sicherheitsdaten

wgk
3
tsca
TSCA listed
ridadr
UN 3276 6.1/PG 2
hs_code
29269095
RTECS-Nr.
UG1400000
risk_code
23-28
Toxizität
LD50 orally in mice, rats: 9, 100 mg/kg, Fassett in Industrial Hygiene and Toxicology vol. 2, F. A. Patty, Ed. (Interscience, New York, 2nd ed., 1962) pp 2025-2026
hazard_code
T+
safety_code
36/37/39-45
hazard_class
6.1
packing_group
II
Speicherklasse
6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
Giftige Stoffe Daten
542-76-7(Hazardous Substances Data)
Hazard Classifications
Acute Tox. 2 OralEye Irrit. 2Skin Irrit. 2
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