기본 정보
- 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
이름 더 보기
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
Odor
Odorless
Odor similar to that of hydrogen cyanide
Density
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
Solubility
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
greater than 200 °F (NTP, 1992)
Flash point > 200 °F
Boiling Point
361 °F at 760 mmHg with slight decomposition (EPA, 1998)
183 °C (slight decomp)
183 °C
183 °C @760 [mm Hg]
361 °F (Decomposes)
Melting Point
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
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.
안전 및 규제
GHS 분류
GHS Classification
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
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.
Fire Hazards
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.
안전 및 보호
Fire Fighting
(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
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
Warning: Formaldehyde cyanohydrin exposure by any route (oral, dermal, inhalation) may produce cyanide poisoning.
(General first aid procedures)
Disposal Methods
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
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
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.
독성 정보
Interactions
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/
Environmental Fate
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).
Exposure Routes
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
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
Soil Adsorption/Mobility
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
... 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.
Environmental Bioconcentration
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
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
CERCLA Reportable Quantities
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)
화학 및 산업
약리 정보
Metabolism/Metabolites
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/
용도 및 제조
Uses
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
2023: 10,000,000 - <50,000,000 lb
(1972) PROBABLY GREATER THAN 9.08X10+5 G
(1975) PROBABLY GREATER THAN 4.54X10+5 G
Methods of Manufacturing
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.
General Manufacturing Information
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
하류 제품
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