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포름알데히드 시아노히드린

Hydroxyacetonitrile

HCID 7857
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기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
부분 구조 검색유사 구조 찾기

기본 정보

CAS
107-16-4
표준 SMILES
N#CCO
InChIKey
LTYRAPJYLUPLCI-UHFFFAOYSA-N
분자식
C2H3NO
평균 분자량
57.05 g/mol
단동위원소 질량
57.02146372

개요

Formaldehyde cyanohydrin is an odorless colorless oil with a sweetish taste. Used in the manufacture of intermediates in pharmaceutical production, as a component of synthetic resins, as a chemical intermediate for organic compounds, and as a solvent. (EPA, 1998)

이름 및 식별자

우선 이름
Hydroxyacetonitrile
IUPAC
2-hydroxyacetonitrile
현지명
포름알데히드 시아노히드린
영어명
Glycolonitrile
분자식
C2H3NO
분자량
57.05

이름 및 동의어

GLYCOLONITRILEHydroxyacetonitrile2-HydroxyacetonitrileCyanomethanolGlycolic nitrile107-16-4Formaldehyde cyanohydrinGlyconitrileGlycollonitrile2-HydroxyethanenitrileHydroxymethylnitrileHydroxyactonitrile
이름 더 보기
포름알데하이드시아노히드린포름알데히드시아노히드린포름알데하이드시아노히드린HOCH2CNusafa-8565
Acetonitrile, hydroxy-GlykolonitrilMethylene cyanohydrinUSAF A-8565HydroxymethylkyanidHydroxyazetonitrilalpha-HydroxymethylcyanideAcetonitrile, 2-hydroxy-

데이터베이스 식별자

CAS
107-16-4
PubChem CID
7857
DTXSID
DTXSID3025417
ChEBI
CHEBI:137685
UNII
ZCI474BE63
EC Number
203-469-1
Nikkaji
J4.058D

물성

구조 계산 물성

XLogP
-0.7
극성 표면적
44 Ų
수소 결합 공여자 수
1
수소 결합 수용자 수
2
회전 가능 결합 수
0
무거운 원자 수
4
형식 전하
0
복잡도
41.2

실험 및 물리화학적 성질

Chemical ClassesNitrogen Compounds -> Nitriles
SpringerMaterials PropertiesElectric dipole moment
LogP-1.6
Odor · 2건

Odorless

Odor similar to that of hydrogen cyanide

TasteSWEETISH TASTE
Density · 5건

1.1 at 66 °F (NIOSH, 2024) - Denser than water; will sink

1.10

Relative density (water = 1): 1.1

1.1 @25 °C

(66 °F): 1.10

Color/FormCOLORLESS, WATER-WHITE, OILY LIQUID
Solubility · 5건

greater than or equal to 100 mg/mL at 68 °F (NTP, 1992)

Very soluble in water, ethanol, and ethyl ether; insoluble in benzene.

Soluble in water, ethanol, and diethyl ether but insoluble in chloroform and benzene.

Solubility in water: good

Soluble

Flash Point · 2건

greater than 200 °F (NTP, 1992)

Flash point > 200 °F

Boiling Point

안전 및 규제

안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.

GHS 분류

GHS Classification · 6건

Danger

H300 (100%): Fatal if swallowed [Danger Acute toxicity, oral]

P260, P262, P264, P270, P271, P280, P284, P301+P316, P302+P352, P304+P340, P316, P320, P321, P330, P361+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 94 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Danger

H227: Combustible liquid [Warning Flammable liquids]

유해성 정보

Regulatory Information · 2건

Acetonitrile, 2-hydroxy- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Acetonitrile, 2-hydroxy- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Acetonitrile, hydroxy-: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.

DOT LabelPoison
Fire Hazards · 2건

Moderate explosion hazard when exposed to heat or by spontaneous chemical reaction in the presence of alkalies if uninhibited. When heated to decomposition, it emits highly toxic fumes of cyanide and nitrogen oxides. Unstable, may explode on standing. Hazardous polymerization may occur. avoid the presence of alkalis, and exposure to heat. (EPA, 1998)

Combustible.

Health HazardsExtremely toxic, exposure by any route should be avoided; may have fatal consequences; death from asphyxiation may occur similar to that resulting from hydrogen cyanide. (EPA, 1998)
Hazards SummaryCan cause cyanide poisoning by inhalation or skin routes of exposure; [HSDB] A lachrymator; [CHEMINFO] See NITRILES.

화학 및 산업

약리 정보

Metabolism/Metabolites · 1건

IN THE CASE OF ALIPHATIC NITRILES, IT IS PROBABLE THAT HYDROLYSIS TAKES PLACE WITH THE RELEASE OF THE CN GROUP. THE RAPIDITY WITH WHICH THIS PROCESS OCCURS MAY DETERMINE THE RELATIVE TOXICITY OF THE VARIOUS ALIPHATIC NITRILES. /ALIPHATIC NITRILES/

Absorption, Distribution and ExcretionIT IS ABSORBED THROUGH SKIN, AND IF NOT IMMEDIATELY REMOVED, MAY HAVE FATAL CONSEQUENCES.

용도 및 제조

Uses · 3건

Used to produce pharmaceuticals and synthetic resins; [HSDB]

MANUFACTURE OF INTERMEDIATES IN PHARMACEUTICAL PRODUCTION & AS COMPONENT OF SYNTHETIC RESINS

Solvent and organic intermediate

U.S. Production · 3건

2023: 10,000,000 - <50,000,000 lb

(1972) PROBABLY GREATER THAN 9.08X10+5 G

(1975) PROBABLY GREATER THAN 4.54X10+5 G

Industry UsesIntermediate
Methods of Manufacturing · 4건

REACTION OF FORMALDEHYDE AND AQUEOUS SODIUM CYANIDE IN THE PRESENCE OF MINERAL ACID

Formaldehyde and hydrogen cyanide.

Formed in 79.5% yield when 37% formaldehyde is mixed with a stoichiometric amount of aqueous hydrogen cyanide for 1 hr at 2 °C in the presence of sodium hydroxide as a catalyst.

Patents ... describe synthesis by (1) heating formaldehyde with hydrogen cyanide at 250 °C or in the presence of sulfur dioxide at pH 1.5-2.0 in an aqueous medium and (2) by reacting acetonitrile with oxygen and with or without water at high pressure in the presence of various vanadium oxides.

Formulations/PreparationsSupplied commercially as 70% aq soln stabilized with phosphoric acid
General Manufacturing Information

관련 반응

80건
반응 기록 만들기
HRID 1835 반응식
HRID 1835반응물로uspto-grants-1998_03
HRID 10449 반응식
HRID 10449반응물로uspto-grants-2006_08
HRID 10451 반응식
HRID 10451반응물로uspto-grants-2006_08
HRID 100892 반응식
HRID 100892반응물로Training data from https://doi.org/10.1039/C8SC04228D (2/10)
HRID 119865 반응식
HRID 119865반응물로Training data from https://doi.org/10.1039/C8SC04228D (2/10)
HRID 137022 반응식
HRID 137022반응물로Training data from https://doi.org/10.1039/C8SC04228D (9/10)
HRID 162824 반응식
HRID 162824반응물로Training data from https://doi.org/10.1039/C8SC04228D (9/10)
HRID 207925 반응식
HRID 207925반응물로Training data from https://doi.org/10.1039/C8SC04228D (6/10)
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화합물 노트

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· 5건

361 °F at 760 mmHg with slight decomposition (EPA, 1998)

183 °C (slight decomp)

183 °C

183 °C @760 [mm Hg]

361 °F (Decomposes)

DecompositionWhen heated to decomposition it emits toxic fumes of /nitrogen oxide/ and /cyanides/.
Melting Point · 4건

Less than -98 °F (EPA, 1998)

less than -72 °C

-72 °C

<-98 °F

물리화학적 성질

녹는점
-72 °C · -72°C
끓는 점
183 °C · 183°C
밀도
1.076 g/mL · 1.076 g/mL at 20 °C
굴절률
20 · n20/D 1.389
인화점
133 °F · 133 °F
산도 계수 (pKa)
11.31 · 11.31±0.10(Predicted)
수용성
20 °C에서 · 20°C에서 >=10g/100mL
Henry's Law Constant
1.3 · 1.3×100 mol/(m3Pa) at 25℃, HSDB (2015)
Dielectric constant
27 · 27.0(20℃)
안정성
안정적이지만 알칼리와 격렬하게 반응할 수 있습니다. 강한 산화제와 호환되지 않습니다.
InChI
1S/C2H3NO/c3-1-2-4/h4H,2H2
InChIKey
LTYRAPJYLUPLCI-UHFFFAOYSA-N
SMILES
OCC#N
NIST
Acetonitrile, hydroxy-(107-16-4)
EPA
Formaldehyde cyanohydrin (107-16-4)
화학적 성질 · 1건

light yellow liquid (typically available as a concentrated. Glycolonitrile [107-16-4], hydroxyacetonitrile, formaldehyde cyanohydrin, HOCH2CN, Mr 57.05, bp 183℃ (slight decomp.), d154 1.104, n20D1.4117. Anhydrous glycolonitrile is a colorless liquid which is miscible with water, ethanol and diethyl ether.

Reactive GroupAlcohols and Polyols
UN ClassificationUN Hazard Class: 6.1; UN Pack Group: II
RCRA RequirementsD003; A solid waste containing glycolonitrile may become characterized as a hazardous waste when subjected to testing for reactivity as stipulated in 40 CFR 261.23, and if so characterized, must be managed as a hazardous waste.
Reactivity AlertsPolymerizable
Reactivity ProfileFORMALDEHYDE CYANOHYDRIN may undergo spontaneous and violent decomposition. Traces of alkali (base) promote violent polymerization [Lewis].
Chemical DangersThe substance may violently polymerize under the influence of traces of acids and bases. This generates fire or explosion hazard. Decomposes on heating. This produces toxic fumes including hydrogen cyanide and nitrogen oxides.
Flammable LimitsCombustible Liquid

안전 및 보호

Fire Fighting · 2건

(Non-Specific -- Acetonitrile) Cool containers with flooding quantities of water. Apply water from as far away as possible. Avoid breathing vapors. Keep upwind. Wear self-contained breathing apparatus. Avoid bodily contact with the material. Wear boots, protective gloves, and goggles.

Use water spray, powder, alcohol-resistant foam, carbon dioxide.

First Aid Measures · 4건

Fresh air, rest. No mouth-to-mouth artificial respiration. Refer for medical attention.

Remove contaminated clothes. Rinse skin with plenty of water or shower. Refer for medical attention .

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Rinse mouth. Give a slurry of activated charcoal in water to drink. Induce vomiting (ONLY IN CONSCIOUS PERSONS!). Refer for medical attention .

First Aid · 2건

Warning: Formaldehyde cyanohydrin exposure by any route (oral, dermal, inhalation) may produce cyanide poisoning.

(General first aid procedures)

Safe StorageSeparated from food and feedstuffs, acids and bases. Cool. Store only if stabilized.
Nonfire Spill Response(Non-Specific -- Acetonitrile) Build dikes to contain flow as necessary. Use water spray to disperse vapors and dilute standing pools of liquid. Avoid breathing vapors. Keep upwind. Avoid bodily contact with the material. (EPA, 1998)
Disposal Methods · 2건

Generators of waste (equal to or greater than 100 kg/mo) containing this contaminant, EPA hazardous waste number D003 must conform with USEPA regulations in storage, transportation, treatment and disposal of waste. /Cyanide cmpd/

A poor candidate for incineration. /Cyanides/

Spillage Disposal · 1건

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. Wash away remainder with plenty of water. Do NOT let this chemical enter the environment. Personal protection: complete protective clothing including self-contained breathing apparatus.

Preventive Measures · 5건

The worker should immediately wash the skin when it becomes contaminated.

Work clothing that becomes wet or significantly contaminated should be removed and replaced.

Workers whose clothing may have become contaminated should change into uncontaminated clothing before leaving the work premises.

All nitriles should be handled under carefully controlled conditions and only by personnel having a thorough understanding and knowledge of safe handling techniques. Because of the nature of nitrile cmpd and the lack of complete toxicity data on many nitriles, care should be exercised in handling these cmpd to avoid inhalation of the vapors, ingestion, and contact with the skin. /Nitriles/

For more Preventive Measures (Complete) data for GLYCOLONITRILE (7 total), please visit the HSDB record page.

Isolation and EvacuationExcerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:
Eye PreventionWear face shield or eye protection in combination with breathing protection.
Fire PreventionNO open flames.
Inhalation RiskNo indication can be given about the rate at which a harmful concentration of this substance in the air is reached on evaporation at 20 °C.

독성 정보

Interactions · 1건

The toxic mechanism of nitriles (including propionitrile) and the effect of metabolic modifiers in mice were studied in relation to their physicochemical properties. All the test nitriles liberated cyanide both in vivo and in vitro, with the exception of benzonitrile, although the extent of liberation and the effect of carbon tetrachloride pretreatment on the mortality of animals differed among nitriles. From these results, test compounds were tentatively divided into 3 groups. In group 1, acute toxicity was greatly reduced by carbon tetrachloride pretreatment, in group 2, toxicity was not significantly changed or was somewhat enhanced, and in group 3, benzonitrile only, toxicity was clearly enhanced. The amount of cyanide was higher at death in the brains of mice given group 1 compounds, the level being comparable to that found in mice killed by dosing with potassium cyanide. The relation between log (1/LD50) and log p for the compounds in group 1 fitted a parabolic plot, while that for compounds in group 2 was linear. For most nitriles, the in vitro metabolism was inhibited when the incubation mixture contained either SKF-525A, carbon monoxide, or microsomes from mice treated with carbon tetrachloride. When mice were dosed with ethyl alcohol, metabolic enhancement of nitriles was seen compared with the control. However, ethyl alcohol, when added to the incubation mixture, inhibited the in vitro metabolism of nitriles. /Nitriles/

Target OrgansEyes, skin, respiratory system, central nervous system, cardiovascular system
Environmental Fate · 3건

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 1(SRC), determined from a structure estimation method(2), indicates that glycolonitrile is expected to have very high mobility in soil(SRC). Volatilization of glycolonitrile from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 7.4X10-6 atm-cu m/mole(3). Glycolonitrile is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 0.8 mm Hg(4).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 1(SRC), determined from a structure estimation method(2), indicates that glycolonitrile is not expected to adsorb to suspended solids and sediment in water(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 7.4X10-6 atm-cu m/mole(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 61 hrs and 30 days, respectively(SRC). According to a classification scheme(5), an estimated BCF of 0.5(SRC), from an estimated log Kow of -1.6(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low.

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), glycolonitrile, which has an estimated vapor pressure of 0.8 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase glycolonitrile is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 21 days(SRC), calculated from its rate constant of 7.61X10-11 cu cm/molecule-sec at 25 °C(3).

Adverse EffectsOther Poison - Chemical Asphyxiant
Exposure Routes · 2건

The substance can be absorbed into the body by inhalation, through the skin and by ingestion.

inhalation, skin absorption, ingestion, skin and/or eye contact

Signs and Symptoms · 5건

Dizziness. Lethargy. Headache. Shortness of breath. Weakness. Blue lips, fingernails and skin.

MAY BE ABSORBED! Further see Inhalation.

MAY BE ABSORBED! Redness. Pain. Blurred vision. Further see Inhalation.

See Inhalation.

irritation eyes, skin, respiratory system; headache, dizziness, lassitude (weakness, exhaustion), confusion, convulsions; dyspnea (breathing difficulty); abdominal pain, nausea, vomiting

ICSC Environmental DataThis substance may be hazardous to the environment. Special attention should be given to aquatic organisms.
Soil Adsorption/Mobility · 1건

Using a structure estimation method based on molecular connectivity indices(1), the Koc for glycolonitrile can be estimated to be about 1(SRC). According to a classification scheme(2), this estimated Koc value suggests that glycolonitrile is expected to have very high mobility in soil.

Human Toxicity Excerpts · 5건

... STUDIES ... INDICATE THAT IT IS A HIGHLY TOXIC SUBSTANCE & EXPOSURE BY ANY ROUTE MUST BE STRICTLY AVOIDED. DIRECT CONTACT WITH EXPOSED SKIN GIVES NO IMMEDIATE /SENSATION/. IT IS ABSORBED THROUGH SKIN, & IF NOT IMMEDIATELY REMOVED, MAY HAVE FATAL CONSEQUENCES.

EXPOSURE TO TOXIC NITRILES MAY RAPIDLY CAUSE DEATH BY ASPHYXIATION SIMILAR TO THAT RESULTING FROM ... HYDROGEN CYANIDE. /NITRILES/

BEECH-NUT MEAL CONTAMINATED WITH GLYCOLONITRILE LED TO PROLONGED DEADLY POISONING WITH HYDROCYANIC ACID IN 3 PERSONS. HISTOTOXIC HYPOXYDOSIS WAS EXPRESSED BY SYMMETRIC NECROSIS OF NUCLEUS LENTIFORMIS WHICH WAS DISTINGUISHABLE FROM OTHER HISTOLOGICAL BRAIN CHANGES.

NITRILES ARE ORG CYANIDES. ACRYLONITRILE, PROPIONITRILE & SOME OTHERS RESEMBLE CYANIDES IN TOXICITY. OTHER NITRILES SUCH AS CYANAMIDES & CYANATES HAVE NO CYANIDE EFFECT. /NITRILES/

For more Human Toxicity Excerpts (Complete) data for GLYCOLONITRILE (8 total), please visit the HSDB record page.

Artificial Pollution SourcesGlycolonitrile's production and use as a solvent and organic intermediate(1) may result in its release to the environment through various waste streams(SRC).
Environmental Bioconcentration · 1건

An estimated BCF of 0.5 was calculated for glycolonitrile(SRC), using an estimated log Kow of -1.6(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low.

Volatilization from Water/Soil · 1건

The Henry's Law constant for glycolonitrile is estimated as 7.4X10-6 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that glycolonitrile is not expected to volatilize from water surfaces(2). 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)(2) is estimated as 61 hrs(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(2) is estimated as 30 days(SRC). Glycolonitrile's Henry's Law constant(1) indicates that volatilization from moist soil surfaces may occur(SRC). Glycolonitrile is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 0.8 mm Hg(3).

규제 정보

RCRA RequirementsD003; A solid waste containing glycolonitrile may become characterized as a hazardous waste when subjected to testing for reactivity as stipulated in 40 CFR 261.23, and if so characterized, must be managed as a hazardous waste.
CERCLA Reportable Quantities · 1건

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. Formaldehyde cyanohydrin 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.

안전 데이터

OEL
Ceiling: 2 ppm (5 mg/m3) [15-minute]
wgk
-
tsca
TSCA listed
rtecs
AM0350000
ridadr
UN 3276 6.1/PG 1
독성
mouse,LCLo,inhalation,27ppm/8H (27ppm),BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)SENSE ORGANS AND SPECIAL SENSES: LACRIMATION: EYE,"Toxicology of Drugs and Chemicals," Deichmann, W.B., New York, Academic Press, Inc., 1969Vol. -, Pg. 290, 1969.
risk_code
26/27/28
hazard_code
T+
safety_code
36/37/39-45-36/37-28
포장분류
I
위험 등급
6.1(a)
Hazard Classifications
Acute Tox. 2 DermalAcute Tox. 2 InhalationAcute Tox. 2 Oral
스토리지 클래스
6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
유해 물질 데이터
107-16-4(Hazardous Substances Data)
· 2건

All Other Basic Organic Chemical Manufacturing

Acetonitrile, 2-hydroxy-: ACTIVE

응용 분야

용도Solvent and organic intermediate.

일반 설명Odorless colorless oil with a sweetish taste. Used in the manufacture of intermediates in pharmaceutical production, as a component of synthetic resins, as a chemical intermediate for organic compounds, and as a solvent.

제조 방법

생산 방법Glycolonitrile is the result of reaction between formaldehyde and aqueous sodium cyanide in the presence of mineral acid.

상·하류 제품 정보

상류 원료

dilute sulphuric acidformaldehydePotassium hydroxide solution시안화수소사이안화 칼륨

하류 제품

FENPYRITHRINN-메틸아미노촨나트륨만데릭산메톡시아세토닐트릴아크릴산부탄이미노 디초산Ethyl 2,3-dicyanopropionate옥사졸-2-아민디에틸아미노아세토니트릴