Basic information
- Standard SMILES
Cc1ccco1- InChIKey
VQKFNUFAXTZWDK-UHFFFAOYSA-N- Molecular formula
- C5H6O
- Average molar mass
- 82.1 g/mol
- Monoisotopic mass
- 82.04186481
Overview
2-methylfuran appears as a clear colorless liquid with an ethereal odor. Flash point -22 °F. Less dense than water and insoluble in water. Hence floats on water. Vapors heavier than air.
Names & identifiers
- Preferred name
- 2-Methylfuran
- IUPAC
- 2-methylfuran
- English name
- 2-Methylfuran
- Molecular formula
- C5H6O
- Molecular weight
- 82.1
Names & synonyms
2-METHYLFURAN534-22-5SilvanSylvan2-Methyl furanFuran, 2-methyl-5-Methylfuranalpha-Methylfuran2-METHYL-FURANDTXSID902561151O3BGW3F2NSC-3707
Show more names
MEF2-methylfuraneFuran,2-methyl-FEMA 41792-methyl-furaNSC 3707NSC 5211
DTXCID405611FEMA NO. 4179CHEBI:88912RefChem:88322208-594-5MethylfuranFuran, methyl-.alpha.-Methylfuran
Database identifiers
- CAS
27137-41-3、534-22-5- PubChem CID
- 10797
- DTXSID
DTXSID9025611- ChEMBL
CHEMBL1445555- ChEBI
CHEBI:88912- UNII
- 51O3BGW3F2
- EC Number
- 208-594-5、248-253-8
- Nikkaji
- J6.337A
Properties
Computed structural properties
- XLogP
- 1.8
- Topological polar surface area
- 13.1 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 1
- Rotatable bonds
- 0
- Heavy atoms
- 6
- Formal charge
- 0
- Complexity
- 43.2
Experimental & physicochemical properties
Chemical Classes
Other Classes -> Ethers, Other
Flammable agents - 3rd degree
SpringerMaterials PropertiesSchoenflies notation
LogP
1.85
1.85
Food AdditivesFLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Density
0.9132 at 68 °F (NTP, 1992) - Less dense than water; will float
0.908-0.917
0.827 @ 20°C
Flavoring AgentsEU Flavoring substances
Solubility
less than 1 mg/mL at 72.5 °F (NTP, 1992)
3 mg/mL at 20 °C
Slightly soluble in water
Soluble (in ethanol)
Flash Point-22 °F (NTP, 1992)
Boiling Point
145 to 151 °F at 760 mmHg (NTP, 1992)
64 °C
63.7 °C @760 [mm Hg]
Melting Point
-127.7 °F (NTP, 1992)
-87.5 °C
-88.7 °C
Vapor Density2.8 (NTP, 1992) - Heavier than air; will sink (Relative to Air)
Vapor Pressure
59 mmHg at 32 °F ; 95 mmHg at 50 °F; 142 mmHg at 68 °F (NTP, 1992)
142.0 [mmHg]
139 [mm Hg] @20 °C
Physicochemical properties
- Melting point
- -88.7 °C · -88.7 °C
- Boiling point
- 63 · 63-66 °C (lit.)
- Density
- 0.91 g/mL · 0.91 g/mL at 25 °C (lit.)
- vapor density
- 2.8 · 2.8 (vs air)
- vapor pressure
- 139 mm · 139 mm Hg ( 20 °C)
- refractive index
- 20 · n20/D 1.433(lit.)
- FEMA
- 4179 · 4179 | 2-METHYLFURAN
- FLAVIS Number
- 13.03 · 13.030 | 2-Methylfuran
- Flash point
- 8 °F · −8 °F
- storage temp.
- 30 °C · Store below +30°C.
- solubility
- 3000 mg/l · 3000mg/l
- form
- Liquid
- color
- Clear yellow
- Odor
- 1 % · at 1.00 % in propylene glycol. ethereal acetone chocolate
- Odor Type
- chocolate
- biological source
- synthetic
- Water Solubility
- 0.3 g/100 · 0.3 g/100 mL (20 ºC)
- FreezingPoint
- -88.68 ℃ · -88.68℃
- JECFA Number
- 1487 · 1487
- BRN
- 103733 · 103733
- Henry's Law Constant
- 1.5 · 1.5×10-3 mol/(m3Pa) at 25℃, Wieland et al. (2015)
- Stability
- Volatile
- InChI
- 1S/C5H6O/c1-5-3-2-4-6-5/h2-4H,1H3
- InChIKey
- VQKFNUFAXTZWDK-UHFFFAOYSA-N
- SMILES
- Cc1ccco1
- LogP
- 1.79 · 1.79
- Substances Added to Food (formerly EAFUS)
- 2 · 2-METHYLFURAN
- CAS DataBase Reference
- 534 · 534-22-5(CAS DataBase Reference)
- FDA UNII
- 51 O3BGW3F2 · 51O3BGW3F2
- NIST Chemistry Reference
- 2 · Furan, 2-methyl-(534-22-5)
- EPA Substance Registry System
- 2 · 2-Methylfuran (534-22-5)
- UNSPSC Code
- 12352100 · 12352100
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 2 · GHS02,GHS06
- Signal word
- Danger
- Hazard statements
- 330 · H330-H301-H320-H225
- Precautionary statements
- 501 · P501-P270-P240-P260-P210-P233-P243-P241-P242-P271-P264-P280-P284-P370+P378-P337+P313-P305+P351+P338-P303+P361+P353-P301+P310+P330-P304+P340+P310-P403+P233-P403+P235-P405
- PPE
- Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
- Hazard Codes
- F,T
- Risk Statements
- 11 · 11-23-23/24/25-2017/11/23
- Safety Statements
- 16 · 16-33-45-7/9-9
- RIDADR
- 2301 · UN 2301
- WGK Germany
- 1 · 1
- RTECS
- 2625000 · LU2625000
- TSCA
- TSCA listed
- HazardClass
- 3 · 3
- PackingGroup
- II
- HS Code
- 29321900 · 29321900
- Storage Class
- 3 · 3 - Flammable liquids
- Hazard Classifications
- 2 InhalationAcute · Acute Tox. 2 InhalationAcute Tox. 3 OralFlam. Liq. 2
- Toxicity
- 50 orally · LD50 orally in Rabbit: 167 mg/kg
- REACH Registrations
- Active
- Limited Quantities
- 1 L · 1.0 L (0.3 gallon) (liquid)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml)
Safety & regulation
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 0.2% (1 of 468) of reports.
Danger
H225 (99.8%): Highly Flammable liquid and vapor [Danger Flammable liquids]
P210, P233, P240, P241, P242, P243, P260, P261, P264, P264+P265, P270, P271, P273, P280, P284, P301+P316, P303+P361+P353, P304+P340, P305+P351+P338, P316, P320, P321, P330, P337+P317, P370+P378, P391, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 468 reports by companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Danger
Hazard information
Regulatory Information
Chemical: Furan, 2-methyl-
Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)
Furan, 2-methyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Furan, 2-methyl- 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)
Status: Active Update: 30-05-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/26140
2-Methylfuran: 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 LabelFlammable Liquid
Fire Hazards
Excerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]:
· HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames.
Health Hazards
Excerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]:
CAUTION: Petroleum crude oil (UN1267) may contain TOXIC hydrogen sulphide gas.
Hazards Summary
Causes liver changes and somnolence in inhalation studies of rats; [RTECS] Furan-substituted aliphatic hydrocarbons have not been evaluated for safe use as flavoring agents due to unresolved toxicological concerns, mainly being the carcinogenicity of furan in animal experiments; [JECFA] Contains 0.024% BHT (CAS# 128-37-0) as a stabilizer; May cause irritation; Toxic by inhalation; [Sigma-Aldrich MSDS] See Furan.
DOT ID and Guide2301 128
Reactive GroupEthers
Reactivity AlertsHighly Flammable
Reactivity Profile2-METHYLFURAN is incompatible with strong acids and strong bases. May react vigorously with oxidizing materials (NTP, 1992).
DOT Hazard Classification
2-Methylfuran
UN2301
Class 3 Flammable and combustible liquid (49 eCFR § 173.120)
PG II: the degree of danger presented by the material is medium
Air and Water ReactionsHighly flammable. Insoluble in water.
Hazard Classes and Categories
Flam. Liq. 2 (99.8%)
Flammable liquids - Category 2
Flammable agents - 3rd degree, Reactive agents - 1st degree
Safety & protection
Fire FightingExcerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]:
Accidental Release Measures
· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.
· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.
First Aid
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.
General First Aid:
Exposure Control and Personal Protection· Wear positive pressure self-contained breathing apparatus (SCBA).
Nonfire Spill ResponseExcerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]:
Isolation and Evacuation
Excerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]:
Immediate precautionary measure
Protective Action Criteria (PAC)
0.33 [ppm]
3.7 [ppm]
22 [ppm]
Personal Protective Equipment (PPE)Excerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]:
Emergency Response Planning GuidelinesCAUTION: The majority of these products have a very low flash point. Use of water spray when fighting fire may be inefficient.
Toxicology
Adverse EffectsNeurotoxin - Acute solvent syndrome
Toxicity DataLC50 (rat) = 500 ppm/4hr
Safety data
- PPE
- Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
- wgk
- 1
- tsca
- TSCA listed
- rtecs
- LU2625000
- ridadr
- UN 2301
- hs_code
- 29321900
- Toxicity
- LD50 orally in Rabbit: 167 mg/kg
- risk_code
- 11-23-23/24/25-2017/11/23
- Signal word
- Danger
- Symbol(GHS)
- GHS02,GHS06
- hazard_code
- F,T
- safety_code
- 16-33-45-7/9-9
- hazard_class
- 3
- Storage Class
- 3 - Flammable liquids
- packing_group
- II
- Hazard statements
- H330-H301-H320-H225
- Limited Quantities
- 1.0 L (0.3 gallon) (liquid)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml)
- REACH Registrations
- Active
- Hazard Classifications
- Acute Tox. 2 InhalationAcute Tox. 3 OralFlam. Liq. 2
- Precautionary statements
- P501-P270-P240-P260-P210-P233-P243-P241-P242-P271-P264-P280-P284-P370+P378-P337+P313-P305+P351+P338-P303+P361+P353-P301+P310+P330-P304+P340+P310-P403+P233-P403+P235-P405
Chemistry & industry
Uses & manufacturing
UsesUsed as flavoring agent or adjuvant; [FDA]
U.S. Production2023: 5,000,000 - <10,000,000 lb
Industry UsesIntermediate
Use Classification
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavoring Agents -> JECFA Flavorings Index
General Manufacturing Information
Pharmaceutical and Medicine Manufacturing
Furan, 2-methyl-: ACTIVE
Applications
Description2-methylfuran is a flammable, water soluble liquid with the potential to be used as an alternative biofuel. It has become very attractive and promising due to the recent breakthrough in its production method through dehydration and hydrogenolysis of fructose or cellulose. This indicates the prospect of industrial mass production of 2-methylfuran and its derivative 2, 5-dimethylfuran. The 2-methylfuran and 2, 5-dimethylfuran have now been considered as a potential choice of alternative fuel pathway for spark ignition (SI) engines because of their similarities to gasoline. Therefore, as an alternative bio-fuels, it presents a potential way to provide sustainable-renewable sources and tackle the severe issue of fossil fuel depletion and global warming.
Uses2-Methylfuran is widely used in manufacturing of drugs like atropine, sodium acetate, furadantine, anisodamine and thiamine furan. In pharmaceuticals industry, synthesis of vitamin B1 is done using 2-Methylfuran. It is less dense than water but its vapors are heavier when contrastedwith air. 2-Methylfuran also finds application as a tool for screening of lung cancer and production of anti-malarial drug like chloroquine. It is also used to produce methyl furfural, aliphatic compounds and sulfur and nitrogen heterocycles. Moreover, 2-Methylfuran is also used for making pesticides, flavors or fragrances and has narcotic effect.
OccurrenceReported found in cooked beef, bread, butter, chicken, cocoa, coffee, currant, mint, tea and tomato.
Uses2-Methylfuran may be used in the synthesis of exo-cis-1-methyl-7-oxabicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic anhydride via Diels-Alder reaction with maleic anhydride.
Uses2-Methylfuran is a volatile organic compound (VOCs) used as a potential non-intrusive tool for screening of lung cancer.
General DescriptionA clear colorless liquid with an ethereal odor. Flash point -22°F. Less dense than water and insoluble in water. Hence floats on water. Vapors heavier than air.
Preparation methods
Preparation2-Methylfuran is an article of commerce (chemical intermediate) and is normally manufactured by catalytic hydrogenolysis of furfural alcohol or via a hydrogenation-hydrogenolysis sequence from furfural in the vapor phase.
Upstream & downstream products
Upstream raw materials
Downstream products
Additional notes
DefinitionChEBI: 2-methylfuran is a member of the class of furans that is furan in which the hydrogen at position 2 is replaced by a methyl group. It has a role as a human urinary metabolite, a hepatotoxic agent, a fuel, a flavouring agent and a plant metabolite. It is a member of furans and a volatile organic compound.
Related reactions
64 records
Linked notes
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