Oleylamine (HCID 5356789)

Overview

promotes fusion of mouse A(9) fibroblasts; RN given refers to parent cpd with unspecified isomeric designation; structure

Names & identifiers

Preferred name: Oleylamine
IUPAC: (Z)-octadec-9-en-1-amine
English name: Oleylamine
Molecular formula: C18H37N
Molecular weight: 267.49

Names & synonyms

OleylamineOleamineOleyl amine112-90-3Armeen OOleinamineNoram OCIS-9-OCTADECENYLAMINEAlamine 11OleylaminKemamine P 9899-Octadecenylamine, (Z)-

Show more names

40%9-OCTADECENYLAMINEeyLAO Vnoramoarmeenoalamine11

(Z)-Octadec-9-enylamineZDQ1JWQ8DTNSC-664611-octadeceneamine hydrofluorideoleoylamineRefChem:577369oleylamine phosphate (1:1), (Z)-204-015-5

Database identifiers

CAS: 112-90-3、1838-19-3
PubChem CID: 5356789
DTXSID: DTXSID8026933
ChEMBL: CHEMBL1976606
UNII: ZDQ1JWQ8DT
EC Number: 204-015-5
Nikkaji: J59.382F

Properties

Computed structural properties

XLogP: 7.6
Topological polar surface area: 26 Å²
Hydrogen bond donors: 1
Hydrogen bond acceptors: 1
Rotatable bonds: 15
Heavy atoms: 19
Formal charge: 0
Complexity: 175

Experimental & physicochemical properties

Chemical ClassesNitrogen Compounds -> Amines, Aliphatic

CosmeticsAntistatic

Vapor Pressure0.0001 [mmHg]

Food Contact SubstancesFCS -> FDA Cumulative Estimated Daily Intake (CEDI)

Physical Description · 2 items

Liquid; CBI

Liquid; mp = 10-20 deg C; [IUCLID] Light yellow pasty liquid with an amine-like odor (mp = 15-30 deg C); [ECHA] Slightly beige paste; [MSDSonline]

Collision Cross Section180.2 Å² [M+H]+ [CCS Type: DT; Buffer gas: N2; Ionization: ESI+; Dataset: TOXCAST; Source Identifier: DTXSID8026933]

Physicochemical properties

Melting point: 18 · 18-26 °C (lit.)
Boiling point: 348 · 348-350 °C (lit.)
Density: 0.813 g/mL · 0.813 g/mL at 25 °C (lit.)
vapor pressure: 8 mm · 8 mm Hg ( 135 °C)
refractive index: 20 · n20/D 1.4596(lit.)
Flash point: 310 °F · 310 °F
storage temp.: Keep in dark place,Inert atmosphere,Room temperature
form: liquid
pka: 10.67 · 10.67±0.10(Predicted)
color: colorless
Odor: slt amine/lemon odor
Water Solubility: insoluble
BRN: 1723960 · 1723960
Stability: Stable. Incompatible with acids, acid chlorides, acid anhydrides, oxidizing agents.
Cosmetics Ingredients Functions: ANTISTATIC
InChI: 1S/C18H37N/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19/h9-10H,2-8,11-19H2,1H3/b10-9-
InChIKey: QGLWBTPVKHMVHM-MDZDMXLPSA-N
SMILES: [H]\C(CCCCCCCC)=C(/[H])CCCCCCCCN
LogP: 7.78 · 7.780 (est)
CAS DataBase Reference: 112 · 112-90-3(CAS DataBase Reference)
EWG's Food Scores: 1 · 1-3
FDA UNII: 1 JWQ8DT · ZDQ1JWQ8DT
EPA Substance Registry System: Oleylamine (112-90-3)
UNSPSC Code: 12352116 · 12352116
NACRES: 23 · NA.23
Symbol(GHS): 5 · GHS05,GHS07,GHS08,GHS09
Signal word: Danger
Hazard statements: 302 · H302-H304-H314-H335-H373-H410
Precautionary statements: 260 · P260-P280-P301+P310-P303+P361+P353-P304+P340+P310-P305+P351+P338
target organs: Respiratory system
PPE: 3 · Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges
Hazard Codes: C,N
Risk Statements: 34 · 34-22-50/53
Safety Statements: 26 · 26-36/37/39-45-24/25
RIDADR: 2735 · UN 2735 8/PG 2
WGK Germany: 2 · 2
RTECS: 4130000 · RG4130000
TSCA: TSCA listed
HazardClass: 8 · 8
PackingGroup: III
HS Code: 29215900 · 29215900
Storage Class: 8 A · 8A - Combustible corrosive hazardous materials
Hazard Classifications: 4 OralAquatic · Acute Tox. 4 OralAquatic Acute 1Aquatic Chronic 1Asp. Tox. 1Eye Dam. 1Skin Corr. 1BSTOT RE 2STOT SE 3
Hazardous Substances Data: 112 · 112-90-3(Hazardous Substances Data)
Toxicity: 50 intraperitoneal · LD50 intraperitoneal in mouse: 888mg/kg
Limited Quantities: 1 L · 1.0 L (0.3 gallons) (liquid) or 1 Kg (2.2 lbs) (solid)
Excepted Quantities: Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml)

Safety & regulation

GHS classification

GHS Classification · 6 items

Danger

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

P260, P261, P264, P270, P271, P273, P280, P301+P316, P301+P317, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P319, P321, P330, P331, P363, P391, P403+P233, P405, and P501 (click each P-code to see the statement)

This chemical does not meet GHS hazard criteria for 3.7% (60 of 1620) of reports.

Danger

H302 (90.6%): Harmful if swallowed [Warning Acute toxicity, oral]

Hazard information

Regulatory Information · 3 items

Chemical: 9-Octadecen-1-amine, (Z)-

9-Octadecen-1-amine, (9Z)- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 9-Octadecen-1-amine, (9Z)- 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)

Oleyl amine: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationIMAP assessments - Primary aliphatic (C12-22) and fatty amines: Human health tier II assessment

Hazards Summary · 1 item

Concentrations of 1.5% and 3% in corn oil produced moderate to severe skin irritation in rats; Post-implantation mortality observed in mice following single oral dose on ninth day of pregnancy; No evidence of teratogenicity in rats or rabbits at gavage doses maternally toxic; No evidence of mutagenicity; [IUCLID] Corrosive to rabbit skin; Effects in 28-day gavage study with rats include abnormal gait, decrease in weight gain, and minor toxicity to the liver and kidneys; No histopathological effects observed in reproductive organs; No evidence of mutagenicity, teratogenicity, or developmental toxicity; [ECHA] Causes burns; Harmful by ingestion, inhalation, and skin absorption; Inhalation can cause corrosive effects on the upper respiratory tract and lungs; [Aldrich MSDS]

DOT Hazard Classification · 2 items

Oleylamine

Marine pollutant

Hazard Classes and Categories · 4 items

Acute Tox. 4 (90.6%)

Acute toxicity - category 4

Acute toxicity (Oral) - Category 4

Acute Tox. 4

Toxicology

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.

TSCA Test Submissions · 1 item

The mutagenicity of (Z)-9-octadecenylamine (ODA) was evaluated in Salmonella tester strains TA98, TA100, TA1535, TA1537 and TA1538, both in the presence and absence of added metabolic activation by Aroclor-induced rat liver S9 fraction. Based on preliminary bacterial toxicity determinations, ODA, diluted with acetone, was tested for mutagenicity at concentrations up to 20 ug/plate for nonactivated cultures and concentrations up to 200 ug/plate for activated cultures using the plate incorporation method. ODA did not cause a positive response in any of the bacterial tester strains, either with or without metabolic activation.

Safety data

PPE: Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges
wgk: 2
tsca: TSCA listed
rtecs: RG4130000
ridadr: UN 2735 8/PG 2
hs_code: 29215900
Toxicity: LD50 intraperitoneal in mouse: 888mg/kg
risk_code: 34-22-50/53
Signal word: Danger
Symbol(GHS): GHS05,GHS07,GHS08,GHS09
hazard_code: C,N
safety_code: 26-36/37/39-45-24/25
hazard_class: 8
Storage Class: 8A - Combustible corrosive hazardous materials
packing_group: III
target organs: Respiratory system
Hazard statements: H302-H304-H314-H335-H373-H410
Limited Quantities: 1.0 L (0.3 gallons) (liquid) or 1 Kg (2.2 lbs) (solid)
Excepted Quantities: Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml)
Hazard Classifications: Acute Tox. 4 OralAquatic Acute 1Aquatic Chronic 1Asp. Tox. 1Eye Dam. 1Skin Corr. 1BSTOT RE 2STOT SE 3
Precautionary statements: P260-P280-P301+P310-P303+P361+P353-P304+P340+P310-P305+P351+P338
Hazardous Substances Data: 112-90-3(Hazardous Substances Data)

Chemistry & industry

Uses & manufacturing

Uses · 6 items

Used as an intermediate, surfactant in textile production, and cosmetic ingredient; Amine and organic salts: Used as petroleum product and lubricant additives, corrosion inhibitors (i.e. in oil fields), ore flotation reagents, wetting agents for asphalt, and emulsifiers; [HSDB] Used in the EU as intermediate, flotation agent for metals, lubricant in metal processing, fuel additive, corrosion inhibitor, and antistatic agent for paints; [ECHA]

Petroleum Production and Refining [Category: Industry]

...SERIES OF PRIMARY, SECONDARY, & ALIPHATIC AMINES, ORG SUBSTITUTED AMMONIA DERIV.../USED AS/ CORROSION INHIBITORS, ORE FLOTATION AGENTS, TEXTILE FINISHING AGENTS, ASPHALT ANTISTRIPPING AGENTS, RUBBER COMPOUNDING, COLOR PARTICLE DISPERSION, PETROLEUM PRODUCT ADDITIVES, CHEMICAL INTERMEDIATES /ALAMINE/

...SERIES OF STRAIGHT CHAIN AMINES...FROM C12 THROUGH C22... /WHICH/ ARE STRONGLY HYDROPHOBIC & ARE BIODEGRADABLE. .../USED AS/ CATIONIC INTERMEDIATES; REMOVAL OF MOISTURE FROM SURFACES /KEMAMINES/

CHEM INT FOR QUATERNARY AMMONIUM SALTS

CHEM INT FOR OLEYL DIAMINE & ETHOXYLATED OLEYLAMINE

U.S. Exports · 2 items

(1979) No Data

(1981) No Data

U.S. Imports · 2 items

(1979) No Data

(1981) No Data

U.S. Production · 3 items

2023: 8,500,000 - <10,000,000 lb

(1979) 2.24X10+9 GRAMS

(1981) 2.49X10+9 GRAMS

Consumer UsesOther

Industry UsesIntermediate

Applications · 4 items

Usesoleamine is an anti-static agent that can be synthetically manufactured or naturally derived.

UsesOleylamine is a long-chain primary alkylamine broadly used in the synthesis of metallic nanostructures. A variety of metallic nanostructures including Au, Ag, Pt, Pd, and their alloy has been synthesized in the presence of oleylamine. It has several important functions in the synthesis of metallic nanostructure. Oleylamine can simultaneously function as a solvent for the reaction mixture and stabilizing agent for metallic nanostructures. In addition, oleylamine has a boiling point of 364 °C; therefore, it can be used to synthesize metallic nanostructures at high temperatures.

UsesUsed in the chemical synthesis and capping of nanoparticles such as Fe3O4, poly (2-hydroxyethyl methacrylate)-graft-poly (ε-caprolactone), titania, mesoporous silica.

General DescriptionOleylamine (OAm) is a long chain primary alkyamine, that acts as an electron donor at elevated temperatures. OAm exhibits affinity to metals through NH2 functional groups. FTIR spectra of OAm has been reported. Oleylamine acts as strong reducing agent as well as a stabilizer in the synthesis of nanoparticle.