N-Formylmorpholine

HCID 20417CAS 4394-85-8
Substructure searchFind similar structures

Basic information

Standard SMILES
O=CN1CCOCC1
InChIKey
LCEDQNDDFOCWGG-UHFFFAOYSA-N
Molecular formula
C5H9NO2
Average molar mass
115.13 g/mol
Monoisotopic mass
115.06332853

Overview

structure in first source

Names & identifiers

Preferred name
N-Formylmorpholine
IUPAC
morpholine-4-carbaldehyde
English name
4-Formylmorpholine
Molecular formula
C5H9NO2
Molecular weight
115.13

Names & synonyms

4-Formylmorpholine4394-85-84-MorpholinecarboxaldehydeN-FORMYLMORPHOLINEMorpholine, 4-formyl-DTXSID7044427D1E63XO4RHNSC-14833DTXCID5024427RefChem:99981224-518-3morpholine-4-carbaldehyde
Show more names
FormmorpholimeN-FormylmorpholN-Formyl MorpholinTIMTEC-BB SBB0076704-Formylmorpholine>
N-FormylmorfolinMFCD000061704-MorpholinecarbaldehydeN-formyl morpholineN-Formylmorfolin [Czech]formyl morpholineUNII-D1E63XO4RHN-formyhnorpholine

Database identifiers

CAS
4394-85-8
PubChem CID
20417
DTXSID
DTXSID7044427
UNII
D1E63XO4RH
EC Number
224-518-3
Nikkaji
J149.689A

Properties

Computed structural properties

XLogP
-0.6
Topological polar surface area
29.5 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
2
Rotatable bonds
0
Heavy atoms
8

Experimental & physicochemical properties

Chemical ClassesNitrogen Compounds -> Morpholines
SpringerMaterials PropertiesBoiling point
Vapor Pressure0.32 [mmHg]
Physical Description · 2 items

Liquid; CBI

Clear colorless liquid; mp = 20-23 deg C; [Sigma-Aldrich MSDS]

Physicochemical properties

Melting point
20 · 20-23 °C (lit.)
Boiling point
236 · 236-237 °C (lit.)
Density
1.145 g/mL · 1.145 g/mL at 25 °C (lit.)
vapor pressure
0.03 hPa · 0.03 hPa (20 °C)
refractive index
20 · n20/D 1.485(lit.)
Flash point
230 °F · >230 °F

Safety & regulation

GHS classification

GHS Classification · 6 items

Warning

H317 (74.1%): May cause an allergic skin reaction [Warning Sensitization, Skin]

P261, P264+P265, P271, P272, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P333+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 259 reports by companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Warning

H317: May cause an allergic skin reaction [Warning Sensitization, Skin]

Hazard information

Regulatory Information · 5 items

Chemical: 4-Morpholinecarboxaldehyde

4-Morpholinecarboxaldehyde is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 4-Morpholinecarboxaldehyde 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)

PMN - indicates a commenced PMN (Pre-Manufacture Notices) substance.

Status: Active Update: 29-03-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/11158

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

Hazards Summary · 1 item

A mild skin and eye irritant; Oral LD50 (rat) = 6.5 mL/kg; [RTECS] May cause skin sensitization; [ECHA REACH Registrations] Search for (4394-85-8[EC/RN Number]) AND (dermatitis OR allergic OR sensitizer OR sensitization): no results; [PubMed] An eye and mild skin irritant; [Sigma-Aldrich MSDS]

Hazard Classes and Categories · 2 items

Skin Sens. 1 (74.1%)

Skin sensitization - Category 1B

Safety data

PPE
Eyeshields, Gloves, multi-purpose combination respirator cartridge (US)
wgk
3
tsca
TSCA listed
rtecs
QD9694000
hs_code
29349990
Toxicity
LD50 orally in Rabbit: > 7360 mg/kg LD50 dermal Rabbit > 18400 mg/kg

Chemistry & industry

Uses & manufacturing

Uses · 2 items

Used as an intermediate, laboratory reagent, in gas treatment, cleaning agents, and professional and consumer coatings; [ECHA REACH Registrations]

Painting (Pigments, Binders, and Biocides) [Category: Paint]

U.S. Production2023: 75,000 - <500,000 lb
Consumer UsesViscosity modifiers
Industry UsesIntermediate
General Manufacturing Information · 2 items

Computer and Electronic Product Manufacturing

4-Morpholinecarboxaldehyde: ACTIVE

Applications · 4 items

Description4-Formylmorpholine is an excellent non-protonic solvent. It is widely used as a solvent and extractant for aromatics. It is used as a detergent for acid gases. In the field of organic synthesis, it can be used to prepare labelled 14C, 4-(trifluoromethyl)morpholine, 3-alkyl-2-chloro-5,6-dihydrobenzaldehyde, triple-biphenyldialdehyde and phenylpropargyl aldehyde. It plays an important role in the desulphurisation of natural gas, syngas, flue gas and petrol.

Uses4-Formylmorpholine is widely used as a solvent and extracting agent for aromatics. It is used as a scrubbing agent for acidic gases. It is employed in the preparation of adenine hydrochloride labeled with 14C, 4-(trifluoromethyl)morpholine, 3-alkyl-2-chloro-5,6-dihydrobenzaldehyde and terphenyl dialdehyde. It plays an important role in the desulfurization of natural gas, synthetic gas, flue gas and gasoline.

Uses4-Formylmorpholine has been used in the preparation of:adenine hydrochloride labelled with 14Cterphenyl dialdehyde

General DescriptionTreatment of 4-formylmorpholine with sulphur tetrafluoride in the presence of potassium fluoride gives 4-(trifluoromethyl)morpholine in excellent yields. 4-Formylmorpholine reacts with series of 2-alkyl-2-cyclohexen-1-ones in the presence of POCl3 to give the corresponding 3-alkyl-2-chloro-5,6-dihydrobenzaldehydes and allylic alcohols (by-product).

Upstream & downstream products

Suppliers50 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
山东前元高分子材料有限公司18678041314 18765609661 · [email protected]
韶远科技（上海）有限公司021-50795510 4000665055 · [email protected]

Related reactions

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Linked notes

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