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Basic Information
CAS No.: 103-34-4
Name: 4,4'-Dithiodimorpholine
Molecular Structure:
Molecular Structure of 103-34-4 (4,4'-Dithiodimorpholine)
Formula: C8H16N2O2S2
Molecular Weight: 236.359
Synonyms: Morpholine,4,4'-dithiodi- (6CI,7CI,8CI);4,4'-Dithiobis[morpholine];4,4'-Dithiodimorpholine;Accel R;Actor R;Bismorpholine disulfide;Bismorpholino disulfide;DTDM;Deovulc M;Di(4-morpholinyl) disulfide;Morpholine disulfide;Morpholinodisulfide;N,N'-Bismorpholine disulfide;N,N'-Dimorpholinyl disulfide;N,N'-Dithiobis[morpholine];N,N'-Dithiodimorpholine;NSC 65239;Nocmaster R 80E;Rhenocure M;RhenocureM/G;Sanfel R;Sulfasan;Sulfasan DTDM;Sulfasan R;Vanax A;Vulnoc R;Rubber accelerator DTDM;
EINECS: 203-103-0
Density: 1.33 g/cm3
Melting Point: 124-130 °C
Boiling Point: 371.7 °C at 760 mmHg
Flash Point: 154 °C
Solubility: 215mg/L at 20.2℃
Appearance: white to off-white crystalline powder
Risk Codes: 36/37/38
Safety: 26-36/37/39
Transport Information: 25kgs
PSA: 75.54000
LogP: 0.73800
Synthetic route
110-91-8

morpholine

103-34-4

4,4'-dithiodimorpholine

Conditions
ConditionsYield
With disulfur dichloride; sodium phosphate at 20℃; for 2h; Reagent/catalyst; Temperature;95.85%
With disulfur dichloride; sodium hydroxide In dichloromethane; water Cooling with ice;84.7%
With disulfur dichloride; sodium hydroxide In hexane; water 1.) 0 deg C 2.) r.t.;80%
139558-39-7

morpholino dithionitrite

103-34-4

4,4'-dithiodimorpholine

Conditions
ConditionsYield
In hexane; benzene for 0.5h; Heating;74%
110-91-8

morpholine

53402-10-1

thiocamphor

A

5038-11-9

N,N'-thiodimorpholine

B

103-34-4

4,4'-dithiodimorpholine

C

1,11,11-trimethyl-3,4,5,6-tetrathia-tricyclo[6.2.1.0(2,7)]undeca-2(7)-ene

D

1,12,12-trimethyl-3,4,5,6,7-pentathiatricyclo[7.2.1.0(2,8)]dodeca-2(8)-ene

Conditions
ConditionsYield
Stage #1: thiocamphor With disulfur dichloride In dichloromethane at 20℃; for 0.166667h;
Stage #2: morpholine In dichloromethane at 20℃; for 1h;
A 10%
B 60%
C n/a
D n/a
5038-11-9

N,N'-thiodimorpholine

A

16131-52-5

dimorpholinotrisulfide

B

103-34-4

4,4'-dithiodimorpholine

C

16131-53-6

N,N'-tetrathiobismorpholine

Conditions
ConditionsYield
With boron trifluoride diethyl etherate Ambient temperature;A 18%
B 6%
C 24%
110-91-8

morpholine

A

5038-11-9

N,N'-thiodimorpholine

B

103-34-4

4,4'-dithiodimorpholine

Conditions
ConditionsYield
With sulfur; iodine In pyridine Product distribution; Heating; effect of amount of S8; other solvent;
103-34-4

4,4'-dithiodimorpholine

17356-08-0

thiourea

C5H11N3OS3

Conditions
ConditionsYield
In methanol Mechanism; Ambient temperature; also with N,N'-thio- and N,N'-dithiobisamides, other temperature;90%
In methanol Ambient temperature;90%
103-34-4

4,4'-dithiodimorpholine

copper(II) perchlorate hexahydrate

75-05-8

acetonitrile

14057-91-1

tetrakis(acetonitrile)copper(I) perchlorate

Conditions
ConditionsYield
In acetonitrile byproducts: SO2, O(CH2CH2)2NH2ClO4, HClO4; (N2); stirring at ambient temp.; disolution in hot CH3CN; filtration; evapn.; elem. anal.; NMR;88%
103-34-4

4,4'-dithiodimorpholine

2958-89-6

N-(chlorosulfanyl)morpholine

Conditions
ConditionsYield
With sulfuryl dichloride In benzene at 5 - 33℃; for 0.283333h;87.9%
With sulfuryl dichloride In tetrachloromethane at 60℃; for 2h;85%
With chlorine In tetrachloromethane at 0 - 5℃;48%
103-34-4

4,4'-dithiodimorpholine

199620-14-9, 13007-92-6

chromium(0) hexacarbonyl

136921-41-0

Cr(CO)5(O(CH2CH2)2NSSN(CH2CH2)2O)

Conditions
ConditionsYield
In tetrahydrofuran Irradiation (UV/VIS); under purified nitrogen; irradn. of Cr(CO)6 for 90 min at room temp.; addn. of S2(N(CH2CH2)2O)2, stirring for 1 h; removal of solvent in vacuo; sublimation of excess of Cr(CO)6; residue dissolved in n-hexane; filtration; concn.; elem. anal.;80%
103-34-4

4,4'-dithiodimorpholine

16131-52-5

dimorpholinotrisulfide

Conditions
ConditionsYield
With tritylsulfenyl chloride In chloroform at 20℃; for 24h;75%
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Chemistry

Molecular Structure of 4,4'-Dithiodimorpholine (CAS NO. 103-34-4):

IUPAC Name: 4-Morpholin-4-yldisulfanylmorpholine 
Molecular Formula: C8H16N2O2S2
Molecular Weight: 236.354840 g/mol
Index of Refraction: 1.619
Molar Refractivity: 62.27 cm3
Molar Volume: 177.4 cm3
Surface Tension: 57.8 dyne/cm
Density: 1.33 g/cm3
Flash Point: 178.6 °C
Enthalpy of Vaporization: 61.87 kJ/mol
Boiling Point: 371.7 °C at 760 mmHg
Vapour Pressure: 1.02E-05 mmHg at 25 °C
Melting Point: 124-125 °C
Storage Temp.: Refrigerator
BRN: 0126214
EINECS: 203-103-0
Product Categories: Rubber Chemicals;Industrial/Fine Chemicals;SULFUR DONOR

Production

  4,4'-Dithiodimorpholine can be get by the reaction of MORPHOLINE and SULFUR chloride.

Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LC50 inhalation 1624mg/m3 (1624mg/m3)   Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 53(3), Pg. 90, 1988.
mouse LD50 intraperitoneal 50mg/kg (50mg/kg)   National Technical Information Service. Vol. AD277-689,
mouse LD50 intravenous 100mg/kg (100mg/kg)   U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#02252,
mouse LD50 oral 1660mg/kg (1660mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 11, Pg. 798, 1961.
rat LD50 oral 4300mg/kg (4300mg/kg)   Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 51(12), Pg. 67, 1986.

Safety Profile

Safety Information of 4,4'-Dithiodimorpholine (CAS NO. 103-34-4):
Risk Statements: 36/37/38
R36/37/38:Irritating to eyes, respiratory system and skin
Safety Statements: 26-36/37/39
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection
RTECS: QE3325000

Specification

  4,4'-Dithiodimorpholine with cas registry number of 103-34-4 is also called Di(morpholin-4-yl) disulphide ; Morpholine, 4,4'-dithiobis- ; N,N'-Bismorpholine disulfide ; N,N'-Dithiodimorfolin ; N,N'-Dithiodimorfolin [Czech] ; N,N-Dithiodimorpholine ; Sanfel R ; Sulfasan ; Sulfasan R ; USAF B-17 ; USAF EK-T-6645 ; Vanax A ; Vulnoc ; Morpholine, 4,4'-dithiodi- . It is applicable to be natural rubber and synthetic rubber.